On Monday, when Chicago Magazine released its third annual list of the “100 Most Powerful Chicagoans,” it explained that, “Influence, ability, and clout decide who ranks where.”

And who ranks at the top of the magazine’s list for 2014 is Rahm Emanuel, although when Chicago’s mayor was asked who he thinks is the most powerful person in town, he responded, “I have no idea. I don’t spend time thinking about it.”

Well, on Monday night, I did spend time thinking about not the most powerful person in town, but rather Chicago’s most powerful sports figure. Among its roll call of political heavyweights, business executives, celebrity restaurateurs and artistic types, Chicago Magazine did place six local sports figures on its 2014 Power List, although four of those six dropped from their spots in last year’s rankings.

Just like wins for their struggling teams, Chicago’s sports bigwigs could apparently use more power. Or perhaps, when it comes to sports, wins and power equate to the same thing. Either way, here are the city’s most powerful sports figures as ranked in Chicago Magazine’s list, along with my own thoughts about each:

What Chicago Magazine says: “The Chicago baron’s overlapping spheres of influence – real estate, his $2 billion spirits distributorship, and sports – make him a perennial power player, but he moves up the list five spots post-Stanley Cup.”

What I say: Considering how low the Blackhawks’ “Q factor” – and attendance numbers – were in Chicago before Rocky’s dad, Bill Wirtz, passed away in 2007, it’s truly remarkable to ponder how popular the NHL franchise is now. In the past seven years, all we’ve seen are two Stanley Cup championships, the emergence of celebrated young stars, tickets that have become the hottest in town and an explosion of Blackhawks apparel among Chicagoans’ wardrobes. It also makes you wonder what we might have seen if Rocky had taken the Blackhawks’ reins from his dad long before he did.

No. 11: JERRY REINSDORF – Chairman, Chicago Bulls and White Sox

What Chicago Magazine says: “It only looked like a horrible year for the Chairman. Sure, Reinsdorf saw the second – second! – season-ending injury to one of his most important assets, Derrick Rose, and no doubt winced as fans spurned his beloved White Sox during a wretched season. But this old-timer’s portfolio is nothing if not diverse. The Bulls broke ground on a $25 million practice complex in June, United Airlines bought another 20 years of naming rights at the United Center and Reinsdorf-backed firms announced deals to build on the Near West Side (five projects, 220 units) and in the West Loop (two buildings, 72 units).”

What I say: Last year, Reinsdorf ranked No. 5 on Chicago’s Power List, while Wirtz was No. 11. This year, the men whose teams share the United Center swapped spots. That’s understandable considering what Wirtz’s Blackhawks accomplished in 2013. But still, when it comes to a power struggle, I’m not sure I’d bet against Reinsdorf – he of the seven championship rings and 33 years of team ownership – inside a boardroom.

No. 23: JAY CUTLER – Quarterback, Chicago Bears

What Chicago Magazine says: “OK, OK, but listen: With Bulls star Derrick Rose sidelined for a second year, this surly, smirking, ‘You really think I give a damn?’ quarterback is suddenly Chicago’s biggest sports celebrity. He’s the most important player on the city’s most watched team, playing the most popular sport in the country. And on Jan. 2, he signed a $126.7 million, seven-year contract, with $54 million guaranteed. Love him or hate him, you cannot deny that Cutler has gone from lightning rod to lightning tower, becoming the most obsessed-over athlete in Chicago. The fact that he doesn’t care just makes people wag their tongues even more.”

What I say: Does apparent indifference to power actually result in power? It’s an interesting thought, and I suppose that with Cutler – who wasn’t even ranked on Chicago Magazine’s list in 2013 – maybe it does. Still, I think when it comes to true power, the magazine is overrating the QB, although, then again, most everyone seems to do that with Cutler. In a perfect world – and with perfect knees – Rose would hold this spot on the list. News flash: It’s not a perfect world.

No. 25: JIM DELANY – Commissioner, Big Ten Conference

What Chicago Magazine says: “Delany is poised to take the wealthiest sports conference in the nation, according to Forbes, and make it even bigger. He brings Maryland and Rutgers into the conference this summer, adding as much as $100 million a year to his $315 million enterprise. The move expands the reach of the conference’s $270 million cable outlet, another Delany creation, into two of the larger TV markets in the country.”

What I say: Somehow – and I’m not quite sure how – Delany saw his Power List ranking fall eight spots from No. 17 a year ago, despite a season in which the Big Ten’s basketball teams excelled and its football programs helped make the wildly rich conference even richer. Perhaps Delany’s power extends too far beyond Chicago for him to be considered that powerful in Chicago. Among national sports figures, his power would almost surely be ranked higher than No. 25.

No. 48: TOM RICKETTS – Chairman and Co-owner, Chicago Cubs

What Chicago Magazine says: “Ricketts owns one of the most powerful sports brands in the universe. And when the Cubs finally play well, the world will likely be watching – and buying – as much of the team as it can. But five years into the Ricketts era, the team enters this season on the heels of the worst two-year record in its history (127 wins, 197 losses). For a franchise that hasn’t won a World Series in over a century, that’s really saying something. Ricketts spent much of 2013 on another just-as-vexing project: negotiating with neighboring rooftop owners over a planned $300 million renovation of his stadium.”

What I say: As chairman of the Chicago Cubs, Ricketts should have immense power. But resembling a 21st-century Mike McCaskey, it doesn’t really seem like he does. Or perhaps it’s simply that Ricketts doesn’t know how to use his power very well, considering how both the mayor’s office and the rooftop owners have vexed him of late. A year ago, Ricketts was ranked No. 45 on Chicago Magazine’s list and with his title, he should be a lot higher. But to be honest, rating him at No. 48 in 2014 may actually be generous.

What Chicago Magazine says: “The Cubs were horrible in 2013 (66 wins, 96 losses), and Epstein’s most significant move – hiring a manager to develop a team stocked with raw talent – was widely perceived as a bust. The new manager, Rick Renteria, missed the introductory news conference due to a bad hip. The bloom is off the rose. Almost.”

What I say: Really, Epstein, in spite of his star power, only has as much real power as Ricketts’ pocketbook allows him. And considering how the Cubs’ owner still doesn’t seem interested in opening his wallet to invest in the franchise’s big league product, Epstein – who ranked No. 56 on the Power List in 2013 – likely won’t be climbing the standings anytime soon. Same goes for the Cubs.